1,1'-Carbonyldiimidazole → 2-Fluoro-4-{[(imidazole-1-carbonyl)-amino]-methyl}-benzoic acid methyl ester

HRID 909110Notes

Reaction equation

HRID 909110 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=1.[C:14](N1C=CN=C1)([N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=[O:15]>CN(C)C=O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH2:2][NH:1][C:14]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[O:15])=[CH:4][C:5]=1[F:13]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57572260Methyl 4-(aminomethyl)-2-fluorobenzoate

Product 1

HCID 670955062-Fluoro-4-{[(imidazole-1-carbonyl)-amino]-methyl}-benzoic acid methyl esterYield 115.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 4-(aminomethyl)-2-fluorobenzoate (106.9 mg, 0.584 mmol) in N,N-dimethyl formamide (4.0 mL) was added 1,1′-carbonyldiimidazole (Aldrich, 98.9 mg, 0.592 mmol). After it was stirred at rt overnight under an argon atmosphere, the reaction mixture was extracted with EtOAc, and washed with water (2×), and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give 2-Fluoro-4-{[(imidazole-1-carbonyl)-amino]-methyl}-benzoic acid methyl ester (187.0 mg) which was used without further purification.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washwashed with water (2×), and saturated NaCl
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c53246ee10b545bfb73843e1a920108c
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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